Heterogeneous Baeyer–Villiger oxidation of ketones using an oxidant consisting of molecular oxygen and aldehydes in the presence of hydrotalcite catalysts

Kaneda, Kiyotomi; Ueno, Shinji; Imanaka, Toshinobu

doi:10.1039/c39940000797

Cited by 69 publications

(27 citation statements)

References 28 publications

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“…As lactones 2 h and 3 h could not be separated on a preparative scale, the absolute configuration of 2 h was assigned by terminating a CHMO Acineto -mediated fermentation after 3 h and comparing the sign for specific rotation to reported data. The conventional chemical oxidation (mCPBA, [24] sodium percarbonate/TFA, [25] or PhCHO/O 2 [26] as oxidant) of norcamphor 1 h usually gives predominantly racemic normal lactone 2 h (6-14 % of abnormal lactone 3 h). However, in a recent study, H 2 O 2 and hydrotalcites as catalysts were shown to regioselectively provide access to abnormal lactone 3 h. [27] …”

Section: Resultsmentioning

confidence: 99%

Regiodivergent Baeyer–Villiger Oxidation of Fused Ketones by Recombinant Whole‐Cell Biocatalysts

2008

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Recombinant Escherichia coli cells expressing monooxygenases of different bacterial origin were evaluated in microbial Baeyer-Villiger oxidations of racemic fused ketones. During the enzymatic oxidation process, both the "normal" lactone generated by migration of the more-substituted carbon atom and/or the "abnormal" lactone resulting from migration of the less-substituted carbon atom can be formed. Depending on the nature of the Baeyer-Villiger monooxygenase, either a regiodivergent biooxygenation to both lactones in high optical purities was observed or essentially racemic "normal" rearrangement product was formed. The complementary behavior of enzymes was found to correlate with our previous observation of clustering of cycloketone-oxidizing proteins into two distinct clusters based on phylogenetic relationship and biocatalyst performance.

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Section: Resultsmentioning

confidence: 99%

Regiodivergent Baeyer–Villiger Oxidation of Fused Ketones by Recombinant Whole‐Cell Biocatalysts

2008

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“…The Mg-Al oxides systems were reported to be effective catalysts for phenol alkylation [11], condensation of nitroaldols to nitroalcohols [12] or epoxidation of various allylic alcohols [13]. Cu-Mg-Al hydrotalcite-like materials were used as catalysts for Bayer-Villiger oxidation of ketones [14]. Their calcined forms were used in the oxidative coupling of phenylethyne [15], adsorption and oxidation of ammonia [16], N 2 O decomposition [17] as well as in decomposition and reduction of nitrogen oxides and sulphur oxides [e.g.…”

Section: Introductionmentioning

confidence: 99%

Thermal transformations of Cu–Mg (Zn)–Al(Fe) hydrotalcite-like materials into metal oxide systems and their catalytic activity in selective oxidation of ammonia to dinitrogen

Jabłońska

Chmielarz

Węgrzyn

et al. 2013

J Therm Anal Calorim

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and Fe 3? in the Me III positions were synthesized by coprecipitation method. Detailed studies of thermal transformation of obtained LDHs into metal oxide systems were performed using high temperature X-ray diffraction in oxidising and reducing atmosphere, thermogravimetry coupled with mass spectrometry and temperature-programmed reduction. The LDH samples calcined at 600 and 900°C were tested in the role of catalysts for selective oxidation of ammonia into nitrogen and water vapour. It was shown that all copper congaing samples presented high catalytic activity and additionally, for the Cu-Mg-Al and Cu-Mg-Fe hydrotalcite samples calcined at 600°C relatively high stability and selectivity to dinitrogen was obtained. An increase in calcination temperature to 900°C resulted in a decrease of their catalytic activity, possibly due to formation of well-crystallised metal oxide phases which are less catalytically active in the process of selective oxidation of ammonia.

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“…121 Hydrotalcites, Mg 10 Al 2 (OH) 24 CO 3 (Chart 3, type A), have been found to show high catalytic activity for the heterogeneous Baeyer-Villiger oxidation of various carbonyl compounds using a combination system of molecular oxygen and benzaldehyde. 123 A possible reaction mechanism of the BaeyerVilliger oxidation can be considered as follows: 124 (i) autoxidation of benzaldehyde with molecular oxygen affording per- …”

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confidence: 99%

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

Kaneda¹,

Ebitani²,

Mizugaki³

et al. 2006

Bulletin of the Chemical Society of Japan

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142

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This account reviews a novel approach to designing high-performance heterogeneous metal catalysts using hydroxyapatites, montmorillonites, and hydrotalcites as macroligands of active metal species for aerobic alcohol oxidations, carbon-carbon bond formations, and one-pot syntheses. The catalytic systems using the above heterogeneous catalysts offer significant benefits in achieving environmentally friendly organic syntheses aiming towards Green and Sustainable Chemistry. Furthermore, the present preparation method for the immobilization of metal species is strikingly simple and allows a strong protocol for creating various nanostructured and functionalized heterogeneous catalysts.Green and Sustainable Chemistry (GSC) is a revolutionary philosophy that aims to bring about a sustainable society by improvement of the safety and environmental aspects of chemical processes and reduction of the risks of chemical products to people and the environment.1 The emphasis is on eliminating waste at the source-primary pollution prevention-rather than finding incremental end-of-pipe solutions. This concept aims to solve the societal problems of the last century associated with the mass production and consumption of materials, and plays a prime role in providing a venous function in society, encouraging reuse and circulation of resources.One of the powerful solutions in the move toward GSC is the replacement of traditional synthetic methods using harmful stoichiometric reagents that produce vast amounts of waste with cleaner and simple catalytic alternatives with high atom efficiency 1a and low E-factors. 1b Catalytic chemistry, therefore, is of ever-increasing importance because catalysis is a key element in material transformations at atomic and molecular levels, which are an essential realm of chemistry and chemical processes.Our approach to GSC is to develop a highly functionalized heterogeneous metal catalyst based on the unique characteristics of natural layered inorganic materials such as hydroxyapatite, montmorillonite, and hydrotalcite, by using them as macroligands for metal species.2 We consider the above inorganic materials to be advanced nano-scaled catalyst supports allowing for the control of the location of catalytically active metal species, which can be found, for example, on the surface, among the layers, or in the interlayer space. Furthermore, these materials are capable of creating catalytically active metal species responsible for targeted organic transformations involving monomers, chain-like species or giant clusters. The creation of well-defined active metal sites on a solid surface, as characterized by X-ray absorption spectroscopy, not only opens up an avenue to materials that boost catalytic performance, but also aids in the understanding of the molecular basis of heterogeneous catalysis. Another advantage of these catalysts is the possibility of a one-pot synthesis based on a cooperative action by several immobilized active species on the solid surface as multifunctional catalysts. The target react...

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Heterogeneous Baeyer–Villiger oxidation of ketones using an oxidant consisting of molecular oxygen and aldehydes in the presence of hydrotalcite catalysts

Abstract: Hydrotalcites catalyse Baeyer-Villiger oxidation of ketones using a com bination oxidant system of molecular oxygen and benzaldehyde t o give high yields of lactones and esters at 40 "C.

Cited by 69 publications

References 28 publications

Regiodivergent Baeyer–Villiger Oxidation of Fused Ketones by Recombinant Whole‐Cell Biocatalysts

Regiodivergent Baeyer–Villiger Oxidation of Fused Ketones by Recombinant Whole‐Cell Biocatalysts

Thermal transformations of Cu–Mg (Zn)–Al(Fe) hydrotalcite-like materials into metal oxide systems and their catalytic activity in selective oxidation of ammonia to dinitrogen

Design of High-Performance Heterogeneous Metal Catalysts for Green and Sustainable Chemistry

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